Diisobutylaluminum hydride → (3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-acetaldehyde

HRID 902694Notes

Reaction equation

HRID 902694 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[C:32]=2[Cl:41])[CH2:16][CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[Cl:41][C:32]1[C:33]([C:37]([F:38])([F:39])[F:40])=[CH:34][CH:35]=[CH:36][C:31]=1[CH2:30][N:15]([CH2:16][CH:17]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:14][CH2:13][CH2:12][O:11][C:7]1[CH:6]=[C:5]([CH2:4][CH:3]=[O:2])[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 10188816Methyl (3-{3-[[2-Chloro-3-(trifluoromethyl)benzyl](2,2-diphenylethyl)amino]propoxy}-phenyl)acetate

Product 1

HCID 86598296(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-acetaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-40 °C

Procedure

A solution of (3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-acetic acid methyl ester (350 mg, 1.68 mmole) in anhydrous toluene (20 ml) was cooled down to −40° C. in a dry ice/acetonitrile bath. DIBAL-H (1.25 ml, 1.5M solution in toluene, Aldrich) was added in a dropwise fashion. The resulting mixture was stirred at −40° C. for 3 hours and then quenched with 0.01N HCl (aq.). The crude material was concentrated in vacuo and then extracted with EtOAc (3×). The combined organic layers were washed with brine (1×), dried over sodium sulfate, filtered and concentrated in vacuo. Preparative HPLC (YMC, 75×30 mm, 25 ml/min, 70-100% CH3CN) afforded the title compound as an oil, 0.15 g (45%). MS(ES) m/e 566.2 (M+).

Workup

  1. customquenched with 0.01N HCl (aq.)
  2. concentrationThe crude material was concentrated in vacuo
  3. extractionextracted with EtOAc (3×)
  4. washThe combined organic layers were washed with brine (1×)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-76c75d8d935a4637abf91434374d38b9
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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